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I ,which the halogenation of the hydrocarbon. is effected a part of the invention in hand.

TED s ATES PATEN OFFICE.

HERBERT H. DOW, 0F MIDLAND, MICHIGAN, ASSIG-N'OIR. TO THE DOW CHEMICAL COMPANY, OF MIDLAND, MICHIGAN, A CORPORATION OF MICHIGAN.

METHOD MAKING HALOGEN DERIVATIVES OF HYDROCARBONS.

No Drawing.

To all whom it may concern:

Be it known that I, HERBERT H. Dow, a citizen of the United States, and a resident of Midland, county of Midland, and State of Michigan, have invented a new and useful Improvement in Methods of Making Halo gen Derivatives of Hydrocarbons, of which the following is a specification, the principle of the invention being herein explained and the best mode in which I have contemplated applying that principle, so as to distinguish it from other inventions.

The object of the resent invention is to provide a method or making a double halogen derivative, for instance, a monochlor-monobrom derivative of a hydrocarbon, with assurance that the derivative will have the desired constitution. At the same time, I greatly simplify and correspondingly reduce the expense of' operation in makin derivatives of this sort.

To t e accomplishment of the foregoing sists of the steps hereinafter fully described and particularly pointed out in the claims, it being understood that the following description discloses but one of various Ways in'which the principle of the invention may be carried out.

By way of illustration,-I shall describe the application of my present improved method to themaking of monchlor-monobromethane from ethylene. As a preliminary step, I bubble chlorin gas through liquid bromin at a predetermined temperamm to give a definitely constituted lvapor mixture, in the present instance one having equal portions of the two halogens named. Under normal pressure conditions, a temperature of 15-20 degrees centigrade will give a vapor mixture of the chlorin and bromin in equal portions. This mixture is then conducted in gaseous form to a cham-.

It will be understood that I do not mean to limit application of my present improved method to the formation of this particular compound, nor is the specific method by Specification of Letters Patent. Pafi gnted J 11119 10, 1919, Application filed May 24, 1917. Serial No. 170,633.

In other words, with certain classes of hydrocarbons, of which benzol is an example, a

catalyzer will be necessary at this stage in the operation of the process. By utilizing.

however, in the halogenation step a vapor properly regulating the.;.temperature of the bath of liquid bromin to get the desired gaseous mixture of the two halogens.

Other modes of applying the principle of my invention may be employed instead of the one explained, change being made as regards the process herein disclosed, provided the step or steps stated by any one of the following claims or the equivalent of such stated step .or steps be employed.

I therefore particularly point out and distinctl claim as my invention 1. he method of making a double halogen derivative of a hydrocarbon, which consists in mixing the vapors of two halogens in such combining proportions as to produce a reaction of both halogens with the hydrocarbon; and then treating the hydrocarbon with such mixture of halogen vapors.

' 2. The method of making a double halogen derivative of a hydrocarbon, which consists in bubbling the one of lower boiling point as a gas through the otherof higher boiling point in the .form of a liquid, at a predetermined temperature, whereby a vapor mixture is formed in such combining proportions as to produce a reaction of both halogens with the hydrocarbon; and then treating the hydrocarbon with such mixture.

' sists in mixing chlorinand bromin vapors proportions as to proin such combinin both halogens with the duce a reaction 0 hydrocarbons; and then treating the hydro-v carbon with such mixture of halogen vapors.

4. The method 'of making a double halogen derivative of a hydrocarbon, which consiststs in bubbling chlorin gas through liquidl bromin at apredetermiued tempereture, whereby a, vapor mixture is formed in such combining proportions as to produce a reaction of both halogens with the hydrocarbon 3 and then treating the hydrocarbon with such mixture of halogen vapors.

5. The methoci of making a. double halogen derivative of a hydrocarbon, which consists in bubbling chiorin gas through liquid bromin at u temperature of 1520 centigrade whereby a vapor mixture having equal portions of such halogens is formed; and then treating the hyuroeurhon therewith whereby the mono-chlor-mono-brom derivative of such hydrocarbon is formed.

6, The method of making mono-chlormono-brom-ethune, which consists in bubbiing chiorin gas through liquid bromin at a temperature of 15-20 centigrude, whereby 2L vapor mixture having equal portions of such haiogens is formed; and then treating ethylene with such mixture, whereby the desired monochlor mono brom ethane is formedu Signed by me, this 12th day of Ma -3 1917. 2

HERBERT H. DQW. 

